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Stay looped in about sales tips, tech, and enablement that help sellers convert more and become top performers.
In this episode, Patrick sits down with David Fox, a 20-year B2B sales veteran who’s led teams across Oracle, Scaleups, and Siemens, and now helps startups scale revenue through his new venture, Ascend Revenue. They dive deep into how to create high-performing sales cultures, what it really takes to win large enterprise deals, and why “selling” might be the wrong word altogether.
David shares candid lessons from the front lines—how to make your team trust each other, how to think like a CFO, and how to stop acting like a seller and start acting like a partner. If you’re a founder or revenue leader thinking about going upmarket, this one’s for you.
David Fox didn’t set out to work in sales. In fact, he originally planned to become a psychiatrist. But after returning to the Bay Area in the early 2000s, he found himself pulled toward the booming tech scene—and quickly realized that many of the skills he’d honed in psychology translated directly into enterprise sales. “I traded the couch for the sales floor,” he jokes.
At the heart of his sales approach is empathy—truly understanding what matters to customers and helping them solve real problems. Whether it’s hiring for his own team or coaching reps, empathy is the first thing he screens for. “People make decisions based on how they feel,” he says. “Then they validate with data.”
That philosophy has stuck with him through two decades in enterprise sales. For David, closing deals isn’t about pitching—it’s about being a trusted advisor. It’s about diagnosing before prescribing.
When asked what separates average sales orgs from high-performing ones, David doesn’t start with strategy or quota coverage. He starts with trust. “If there isn’t psychological safety, you’ll see sandbagging, fake pipeline, low collaboration,” he explains. “You’ll have a broken organization.”
His go-to framework? Patrick Lencioni’s Five Dysfunctions of a Team. At the base: trust. From there, teams can engage in healthy conflict, make committed decisions, hold each other accountable, and ultimately drive results. But trust has to come first—and it has to be modeled by leadership.
That trust shows up in the little things. Do team members speak up when something’s off? Do reps collaborate across deals? Are leaders willing to admit when they’re wrong or ask for help? These signals matter more than any dashboard.
David’s favorite tactic to build this kind of culture? Red light, green light. Each week, team members share one thing that’s working well (green) and one thing that’s broken (red). “It gets people comfortable being honest,” he says. “And it surfaces problems before they fester.”
David is a big believer that go-to-market isn’t just about sales, marketing, and customer success. It starts with product. “Have you built something the market actually wants—and is willing to pay for?” he asks. If not, no amount of sales process will save you.
He’s also bullish on the rise of the CRO role—not as a glorified VP of Sales, but as a true cross-functional integrator. The CRO’s job is to make sure all parts of the revenue engine—product, marketing, sales, and customer success—are working in sync. That alignment matters even more when you’re moving upmarket.
In David’s view, the customer journey doesn’t end when the contract is signed. “You’re not just closing a deal—you’re building a brand ambassador,” he says. And nothing fuels growth more than happy customers talking to their peers.
If you’re selling into large enterprises, you need to start thinking like them. That means understanding how they make decisions, who’s involved, and what risks they’re trying to avoid. According to David, it’s less about selling your product and more about reducing their anxiety.
“CFOs make decisions based on risk mitigation,” he explains. “They’ll pick a less sexy solution if it feels safer.” That’s why great enterprise reps take time to understand each stakeholder’s success criteria. They map out the landscape, engage at multiple levels, and tailor the message to every audience.
It also means learning to speak the language of finance. David recommends every seller get fluent in financial statements, earnings calls, and analyst questions. “If it doesn’t show up on a P&L or help someone get a raise or a bonus, it’s going to be a tough sell.”
And when it comes to legal? Be prepared. Have your paper process tight, understand where you can negotiate, and know when to pull in your execs. “The biggest deals I’ve done included executive alignment—sometimes all the way up to the chairman,” he says.
Founders often see going upmarket as a badge of honor. But David cautions against doing it too soon. “Just because you want to go upmarket doesn’t mean you should,” he says. The first question to ask: does your product meet enterprise needs around compliance, security, and scale?
If the answer is yes, then start small. Test mid-market first. Build muscle before jumping into the deep end. Don’t just throw your SMB reps at Fortune 500 accounts. You need different people, different processes, and a different mindset.
David also encourages founders to look at expanding within their current segment. Upsell better. Reduce churn. Create more value per customer. “Going upmarket is one lever—but it’s not the only one,” he says. “You can often double ACV without leaving your lane.”
And if you are ready? Treat it like a new product launch. Interview your ICP. Validate your assumptions. Align the roadmap. And be patient—big deals take time. Sometimes your first land will be $50K, not $5M. But it’s the right land, with room to expand.
David doesn’t believe in pitching. He believes in helping. Whether it’s guiding a prospect to the right decision, building a culture of trust on your team, or advising founders on how to scale, his approach is grounded in empathy, insight, and experience.
His parting advice to new sellers? Listen more. Get curious. And if you want to build something big—whether it’s a team or a deal—start with trust.
To follow more of David’s work or learn about Ascend Revenue, find him on LinkedIn.
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